1,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one → 1-(1-(8-bromo-9-methyl-9H-purin-6-yl)piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one

HRID 528034Notes

Reaction equation

HRID 528034 reaction equation
[Br:1][C:2]1[N:3]([CH3:12])[C:4]2[C:9]([N:10]=1)=[C:8](Cl)[N:7]=[CH:6][N:5]=2.[O:13]=[C:14]1[N:18]([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[C:17]2[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=2[NH:15]1>C(O)C>[Br:1][C:2]1[N:3]([CH3:12])[C:4]2[C:9]([N:10]=1)=[C:8]([N:22]1[CH2:21][CH2:20][CH:19]([N:18]3[C:17]4[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=4[NH:15][C:14]3=[O:13])[CH2:24][CH2:23]1)[N:7]=[CH:6][N:5]=2

Participants

4

Reactant 2

HCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 114480128-Bromo-6-chloro-9-methyl-9H-purine

Product 1

HCID 668020361-(1-(8-bromo-9-methyl-9H-purin-6-yl)piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-oneYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

8-bromo-6-chloro-9-methyl-9H-purine (175 mg, 0.71 mmol) was combined with 4-(2-keto-1-benzimidazolinyl)piperidine (185 mg, 0.85 mmol) and dissolved in ethanol (2 mL). The resulting solution was warmed to 100° C. in a sealed tube for 15 minutes. A precipitate formed which was collected and washed with ethanol. An amount of 225 mg of a tan solid was isolated, which was 80% pure an indicated by LCMS analysis. A portion of this material was purified by prep HPLC to provide 6 mg of a white solid. 1H NMR (400 MHz, DMSO-d6): δ 10.80 (s, 1H), 8.21 (s, 1H), 7.14-7.00 (m, 1H), 6.88 (m, 3H), 5.38 (s, 2H), 4.48 (m, 1H), 3.62 (s, 3H), 3.13 (s, 2H), 2.25 (m, 2H), 1.78 (m, 2H). EI (MS) for C18H18BrN7O, found 428.

Workup

  1. customA precipitate formed which
  2. customwas collected
  3. washwashed with ethanol

Sources & evidence

ORD record
ord-92e8193a5b5643eb9f17e3039086a33d
Source dataset
uspto-grants-2016_05
Patent number
US09346807B2

Reaction notes

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